188953-93-7

Upstream product

• 171076-03-2 methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-3,2-C-(2'-oxapropan-1'-yl-3'-ylidene)-α-D-arabino-hexopyranoside 

Downstream Products

• 188953-89-1 Bromomethyl-((2R,4aR,6S,8R,9aR,9bS)-6-methoxy-9a-methyl-2-phenyl-4a,6,8,9,9a,9b-hexahydro-4H-cyclopenta[4,5]pyrano[3,2-d][1,3]dioxin-8-yloxy)-dimethyl-silane 
• 188953-90-4 (2R,4aR,6S,6aS,6bS,9aR,10aR,10bS)-6-Methoxy-8,8,10a-trimethyl-2-phenyl-decahydro-1,3,5,9-tetraoxa-8-sila-pentaleno[2,1-a]naphthalene 
• 188953-95-9 (2R,4aR,6S,6aR,6bS,9aR,10aR,10bS)-6-Methoxy-8,8,10a-trimethyl-2-phenyl-decahydro-1,3,5,9-tetraoxa-8-sila-pentaleno[2,1-a]naphthalene 

Relevant academic research and scientific papers

The first example of a highly stereoselective intramolecular radical cyclisation of a cyclopentenol derivative

Silyl methylene radical cyclisation of a β-allylic cyclopentaannulated derivative of glucose leads to a single cis fused tricyclic ring system whereas the same cyclisation of the corresponding a derivative leads to a mixture of cis and trans fused products. These results can be explained by the preference for the formation of the cis fused 5,6-ring system even when this does not involve reaction from the least hindered side of the molecule.